[CH3:1][O:2][C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.Br[CH2:11][C:12]1[C:21]([F:22])=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[C:14]([F:23])[CH:13]=1.C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O>[F:23][C:14]1[CH:13]=[C:12]([CH2:11][O:9][C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)[C:21]([F:22])=[CH:20][C:15]=1[C:16]([O:18][CH3:19])=[O:17]To a solution of 3-methoxyphenol (221 mg, 1.8 mmol) in DMSO (5 mL) was added methyl 4-(bromomethyl)-2,5-difluorobenzoate (Preparation 27, 491 mg, 1.8 mmol) followed by potassium carbonate (491 mg, 3.5 mmol) and the reaction mixture was stirred at room temperature under nitrogen for 18 hours. The mixture was poured into water and extracted with EtOAc (3×20 mL), washed with 1 M aqueous NaOH and water, dried over magnesium sulphate and the solvent removed under reduced pressure to yield the title compound as a solid, which was taken to the next step without further purification (441 mg, 81%).
Loading…
